While many principals appreciate diverse teacher and student cultural backgrounds, culturally competent principals also work to ensure that their stakeholders value this diversity so that schools demonstrate inclusive and respectful environments. Furthermore, teaching practices must respond to students’ cultural spaces and unique learning needs, through instruction that embraces the diverse experiences of underrepresented students. As culturally relevant pedagogy entered the professional conversations of equity, this sparked the need for preparation programmes and professional development of culturally responsive leaders to guide teachers in meeting the needs of underrepresented students. This chapter examines schools’ limited responses to diverse cultures, along with the insufficient approach schools take to promote and maintain student identities that often represent a global microcosm of society. Looking to the future development of principals, this chapter addresses the need for a combination of culturally competent leadership and culturally sustaining leadership through the support of cultural brokers. Two school principals in New Zealand served as exemplars for understanding how cultural brokers might serve as an essential element in increasing culturally sustaining leadership. This unique position will inspire principals of the future to be leaders who are culturally respectful; thus, ensuring practices that appreciate and promote the culture of all children.